Substantive orthooxyazo dyestuffs and process of making same.



an snares rnann'i canton- EUGEN ANDERWERT, HEBMANN FRITZSCHE, HEINRICH SCHOIBEL, OF BASED,

SWITZERLAND, ASSIGNORS TO SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF

BASEL, SWITZERLAND.

SUBSTANTIVE ORTHOOXYAZO DYESTUFFS AND PROCESS OF MAKING SAME.

Specification of Letters Patent.

Patented Oct. 22, 1918.

No Drawing. Original application filed October 7, 1915, Serial No. 54,513. Divided and this application filed April 26, 1917. Serial No. 164,795.

To all whom it may concern:

Be it known that we, EUGEN ANDERWERT, HERMANN FRITZSCHE, and HEINRICH ScHo- BEL, all three chemists and citizens of the Swiss Republic, and residents of Basel, Switzerland, have invented new Substantive Orthooxyazo Dyestuffs and Processes of Making Same, of which the following is a full, clear, and exact specification.

This application is a divisional one of our application for Letters Patent Ser. No. 54513, filed October 7 1915.

We have found that valuable new substantive polyazodyestufl's are obtained by combining 1 mol. of an aromatic tetrazocompound with 1 mol. of an orthooxyazodyestuff able to combine with a further diazogroup and with 1 mol. of a further azodyestufi' component, which can also be an orthooxymonoazodyestuff able to combine with a further diazogroup. As the aromatic tetrazo-compound there can be employe'd the tetrazo-compound derived from benzidin, tolidin, dianisidin, diaminostilbenedisulfonic acid, diaminodiphenylether,

NHC 0 0 115 the 2:5:1z7- aminonaphtholdisulfonic acid soar one of the following derivatives of 2:5:7- aminonaphtholsulfonie acid:

30 lowing examples:

an. 1: AH

k/k/ i I or one of the corresponding derivatives of- 2 5 1 7-aminonaphtholdisulfonic acid.

As orthooxyazodyestufls can be employed those resulting from the combination of the 5 diazoderivatives of an orthoaminophenol compound or of an orthoaminonaphtholcompound with an azodyestutf component able to combine with two diazogroups appertaining to different diazo bodies as for 10 instance one of the above specified 2:5:7- aminonaphtholsulfonic or 2 5: 1: 7-aminonaphtholdisulfonic compounds, the 1:8:4- aminonaphtholsulfonic acid, the 1:823:6- aminonaphtholdisulfonic acid, the 1:815- aminonaphtholsulfonic acid, the 1:8:4z6-

aminonaphthol disulfonic acid, resorcinol, metaaminophenol, metaphenylenediamin, 2 7-dioxynaphthalene, an aminonaphthol, etc. The new dyestuffs are intensely colored powders yielding with concentrated sulfuric acid intensely colored solutions and dissolving in water with colorations which are changed intensely on addition of sodium carbonate or of soda lye and dyeing cotton, wool, silk, mixed goods, straw, Wood and paper various tints, according to. the methods used for the known substantive dyestuffs.

The invention is illustrated by the fol- Example 1: 10.9 kg. orthoaminophenol are diazotized and poured into a solution of 50.4 kg.

. 4O kgfsodium' carbonate in water. The

;.':.-combinat1on being achieved, a'solution of the tetrazoderivative ofQetA kg. dianisidin is poured into the mass. The intermediate product is formed after a short time whereafter a solution of 26 kg. 1 t-naptholsulfonlc acid is added to the mass and the obtained trisazodyestufi isolated in the usual manner. It dyes unmordanted cotton dull blue tints.

Example 2: The monoazodyestufi resulting from the diazoderivative of 18.9 parts orthoaminophenolsulfonic acid and 11 parts resorcinol is added to a soda-alkaline solution of the intermediate product derived from the tetrazoderivative of 18.4 parts benzidin and 24 parts 2 5 7-aminonaphtholsulfonic acid. The combination belng achieved the dyestufi is salted out, separated by filtration, pressed and dried. It dyes unmordanted cotton violet shades.

Instead of the diazophenolderivatives indicated in the examples, for the preparation of the monoazodyestufis, there can be employed the corresponding diazoacidylphenol derivatives which are able to combine more.

easily, the acidylgroup being split off afterward by saponification.

The new dyestuffs are not only suitable for dyeing cotton, wool, silk and mixed goods, straw, wood, paper, leather, etc., like the known substantive dyestufi's, but also for the production of lakes and as parent mateterials for the derivatives.

What we claim is:

- 1. The described process for the manufacture of substantive polyazodyestufi's consisting in combining 1 molecule of an aromatic tetrazocompound with two molecules of azodyestuif components whereof at production of valuable new least one is a molecule of an orthooxyazodyestufi' able'to combine with a further diazogroup.

2. The described process for the manufacture of substantive polyazodyestufi's consistsulting from the combination of an orthooxydiazo-compound with a 2 z 5 7 -aminonaphtholsulfonic compound.

4. The described process for the manufacture of substantive polyazodyestufl's consisting in combining 1 molecule of an aromatic tetrazocompound with 1 molecule of a 2: 5 7- -aminonaphtholsulfonic compound and with 1 molecule 'of an orthooxyazodyestufi able to combine with a further diazo-group.

5. The described process for the manufacture of substantive polyazodyestufls consisting in combining 1 molecule of an aromatic tetrazocompound with 1 molecule of a 2: 5: 7 aminonaphtholsulfonic compound and with 1 molecule of an orthooxyazodyestufi' derived from a 2: 5:7 aminonaphtl1olsulfonic compound.

6. As new products the described substantive polyazodyestuifs derived from an aromatic tetrazocompound. and from an orthooxyazodyestuff ableito combine with a further diazogroup, which constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in water with colorations: which are changed intensively on addition of sodium carbonate or of soda lye, and dye cotton, wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dyestufis.

7. As new products the described substantive polyazodyestufis which derived from an aromatic tetrazocompound and from an orthooxyazodyestufi derived from an orthooxydiazocompound and an aminonaphtholsulfonic compound, constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in water with colorations which are changed intensively on addition of sodium carbonate or of soda lye, and dye cotton, wool, silk, mixed goods, straw, wood and oxyazodyestuff derived from an orthooxydiazocompound and a 2:5:7-aminonaphtholsulfonic compound, constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in water with colorations which are changed intensively on addition of sodium carbonate or of soda lye, and dye cotton, wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dyestufis.

. 9. As new products the described substantive polyazodyestufi's, which derived from an aromatic tetrazocompound, a 2:5:7-aminonaphtholsulfonic compound and an orthooxyazodyestufi able to combine with a -further diazo-group, constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in Water with colorations which are changed intensively on addition of sodium carbonate or of soda lye, and dye cotton, wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dyestufis.

10. As new products the described substantive polyazodyestufi's which derived from an aromatic ,tetrazo-compound, a 2 :5:7- aminonaphtholsulfonic compound and an orthooxyazodyestufi' derived from an orthooxydiazocompound and a 2: 5:7-aminonaphtholsulfonic acid, constitute deep colored powders yielding with concentrated sulfuric acid deep colored solutions and dissolving in water with colorations which are changed intensively on addition of sodium carbonate or of soda lye, and dye cotton, wool, silk, mixed goods, straw, wood and paper various tints according to the methods used for the known substantive dyestufi's.

In witness whereof we have hereunto signed our names this third day of April 1917, in the presence of two subscribing witnesses. 1

Witnesses:

CARL O. SPAINER, ARMAND BRAUN- 

